CN108569970B - Biphenyldiamine type triarylamine compound and organic electroluminescent device comprising same - Google Patents
Biphenyldiamine type triarylamine compound and organic electroluminescent device comprising same Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/58—Naphthylamines; N-substituted derivatives thereof
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- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
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- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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- H—ELECTRICITY
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
Abstract
The invention provides a biphenyl diamine type triarylamine compound, an organic electroluminescent device comprising the compound and application of the compound in a hole transport layer of the organic electroluminescent device. The biphenyl diamine type triarylamine compound has a structure shown in a general formula (I), and better hole mobility can be realized by using the compound, namely, the voltage of a device can be effectively reduced, and the current efficiency can be improved.
Description
Technical Field
The present invention relates to an aromatic amine compound, an organic electroluminescent device comprising the same, and use of the same in an electron transport layer of an organic electroluminescent device. And more particularly, to a high luminous efficiency, low voltage organic electroluminescent device and a triarylamine derivative of biphenyldiamine type realizing the same.
Background
An organic electroluminescent device (OLED) made of an organic electroluminescent material can be used in the fields of solid-state light-emitting full-color display, solid-state lighting and the like, and is known as a next-generation novel display and lighting technology. Typically, an OLED device comprises a light-emitting layer and a pair of opposing electrodes sandwiching the layer. When an electric field is applied between the electrodes, electrons are injected from the cathode side and holes are injected from the anode side, the electrons are recombined with the holes in the light-emitting layer to form an excited state, and energy is released as light when the excited state returns to the ground state.
For OLED display, organic hole transport materials, especially triarylamine hole transport materials, have high photoelectric conversion efficiency due to low toxicity, simple and convenient processing, low price and strong chemical modification, and have very important application value in the leading-edge fields of photoconductors, electroluminescent devices and the like. The triarylamine hole transport material mainly has 6 structural types, such as triphenylamine type, diphenyldiamine type, phenylenediamine type, vinyl arene type, fluorenediamine type, carbazole type and the like. Among them, the biphenyldiamine type and the phenylenediamine type have high melting points, good durability, strong compatibility with resin, high hole transmission efficiency and the most extensive application.
Disclosure of Invention
Currently, organic electroluminescent materials with further improved luminous efficiency are being sought. Patent application documents US20160133847 and US8716484 disclose the following compounds as hole-transporting compounds,
however, when these compounds are used in an organic light-emitting device, the device performance achieved is not sufficient, and there is still a need for a hole-transporting compound having more excellent performance.
In order to solve the above problems, the present invention provides a diarylamine type triarylamine compound having a structure represented by the following general formula (I),
wherein Ar is1、Ar2Independently selected from:
R1、R2independently selected from substituted or unsubstituted C3-C20Aryl, heteroaryl, and combinations thereof, the substituents selected from the group consisting of: halogen atom, alkyl group, cycloalkyl group, heteroalkyl group, aralkyl group, alkoxy group, aryloxy group, amino group, silyl group, alkenyl group, cycloalkenyl group(iii) a heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid group, ester group, nitrile group, isonitrile group, thio group, sulfinyl group, sulfonyl group, phosphino group, or a combination thereof;
R3、R4、R5、R6、R7、R8、R9independently selected from: hydrogen, halogen atoms, substituted or unsubstituted alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, or combinations thereof;
R10、R11selected from alkyl, cycloalkyl, heteroalkyl, aralkyl, aryl, heteroaryl, or combinations thereof;
each R is1、R2、R3、R4、R5、R6、R7、R8Or R9Not mutually connected to form a ring, and not condensed with adjacent benzene rings to form a ring; optionally, R10、R11Can be mutually connected to form a ring;
n represents an integer of 0 to 3, m represents an integer of 0 to 5, p represents an integer of 0 to 7, and q represents an integer of 0 to 4.
When R is3、R4、R5、R6、R7、R8、R9When a plurality of them is present, each of the plurality of them may be the same or different.
The organic electroluminescent device using the arylamine compound as the hole transport material can realize excellent photoelectric properties. Wherein Ar is1、Ar2Independently selected from:
these two groups are essential for achieving excellent luminescence properties in the present invention, and when the specific group is introduced into the triarylamino group, charge transport is facilitated due to the large conjugated structure achieved. The inventor of the invention finds that the balance of carrier transmission can be realized by regulating and controlling the charge transmission performance through the two groups, and the balance greatly improves the luminous efficiency of the device.
In the compound represented by the above general formula (1), R is1、R2Preferably independently at least one substituted or unsubstituted, group selected from phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, indenyl, fluorenyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, furanyl, pyrrolyl, thienyl, carbazolyl, phenothiazinyl, phenoxazinyl, azacarbazolyl,
R3、R4、R5、R6、R7、R8、R9preferably independently at least one substituted or unsubstituted alkyl, cycloalkyl, phenyl, biphenyl, terphenyl, pyridyl, naphthyl, anthryl, phenanthryl, indenyl, fluorenyl, furyl, pyrrolyl,
R10、R11preferably at least one independently substituted or unsubstituted alkyl, cycloalkyl, phenyl, biphenyl, terphenyl, pyridyl, naphthyl, anthryl, phenanthryl, indenyl, fluorenyl, furyl, pyrrolyl.
Further, the present inventors have found that, in the compound represented by the above general formula (1), R is1、R2Further, at least one selected from the group consisting of phenyl, biphenyl, terphenyl, phenanthryl, indenyl, and fluorenyl, which are independently substituted or unsubstituted, is more preferable, because it is presumed that the hole transport material can be arranged more densely and combined more densely on the device by introducing these groups. Therefore, when the novel biphenyl diamine type triarylamine compound is used for an organic electroluminescent device, the device voltage can be effectively reduced, the current efficiency can be improved, and the compound is a hole transport material with very good performance.
R3、R4、R5、R6、R7、R8、R9Further preferably independently substituted or unsubstituted, is selected fromC1-C4Alkyl of (C)3-C6At least one of cycloalkyl, phenyl and biphenyl,
R10、R11further preferably independently substituted or unsubstituted, is selected from C1-C4Alkyl of (C)3-C6At least one of cycloalkyl, phenyl, biphenyl, terphenyl.
Further, the present inventors have found that the compound represented by the above general formula (1) is preferably a centrosymmetric compound, that is, preferably R1And R2Same as R3And R4Same as R5And R6Same as R10And R11The same is true. When the compound of the present invention is a centrosymmetric compound, it is more convenient in synthesis and provides more excellent light-emitting efficiency, which may be due to the fact that the properties of the hole transport material are greatly related to the self-assembly between molecules, and the molecules of the symmetric structure have stronger interaction force between molecules, so that the molecules are more tightly combined and have better transport properties.
Specifically, the compound represented by the above general formula (1) is selected from one of the following compounds:
in addition, the present invention provides an organic hole transport material comprising the compound of the present invention. The invention also relates to an organic electroluminescent device comprising a substrate, a cathode, an anode and a hole transport layer located between the cathode and the anode, the hole transport layer comprising the inventive triarylamine compound of the biphenyldiamine type. The novel triarylamine hole transport material of the biphenyldiamine type has more excellent hole mobility than the existing hole transport material.
In the present invention, the expression of Ca to Cb means that the group has carbon atoms a to b, and the carbon atoms do not include the carbon atoms of the substituents unless otherwise specified.
In the present invention, the expression of chemical elements includes the concept of chemically identical isotopes, such as the expression of "hydrogen", and also includes the concept of chemically identical "deuterium" and "tritium".
Detailed Description
The compound in the above general formula (1) may be used as a hole transport layer material in an organic electroluminescent device, but is not limited thereto.
Specific preparation methods of the compounds of the present invention will be described in detail below by taking a plurality of synthetic examples as examples, but the preparation methods of the present invention are not limited to the plurality of synthetic examples, and those skilled in the art can make modifications, equivalents, improvements, etc. without departing from the principle of the present invention, and extend the methods to the scope of the claims of the present invention.
The arylamine compound represented by the general formula (1) can be used for a hole transport layer of an organic electroluminescent device and can be synthesized by adopting aniline compounds and several special halogenated aromatic hydrocarbons through palladium-catalyzed Buchwald-Hartwig coupling reaction. A representative synthetic route is as follows:
representative synthetic scheme 1: 
wherein Ar is as defined above for Ar1、Ar2Defining; r is as above R1-R6Definition of
Further, specifically synthesized are the following compounds
In a 500mL eggplant type flask, 4-4' -dibromobiphenyl (31.2g,0.1mol), 1-naphthylamine (28.6g,0.2mol), palladium acetate 0.92g, X-phos 1.5g, sodium t-butoxide (29g,0.3mol) and dehydrated toluene 350mL were put under an argon flow, and reacted for 3 hours under reflux. After cooling, water and EA were added for extraction, the organic phase was filtered through celite and concentrated, and the resulting crude product was washed with ethanol to give a pale yellow solid M1 ═ 36.8g, yield 84.5%.
Similarly, we synthesized the intermediates shown in the following table using the same method:
examples of Synthesis of the Main Compounds
Synthesis example 1.
Synthesis of A1
2, 4-diphenylbromobenzene (4.4g,0.01mol), M1(6.2g,0.02mol), palladium acetate 0.26g, X-phos 0.4g, sodium tert-butoxide (2.9g,0.03mol) and dehydrated toluene 100mL were put into a 250mL eggplant-type flask under an argon flow, and reacted for 3 hours under reflux. After cooling, the reaction solution was filtered through celite, and the resulting crude product was recrystallized from toluene to give 6.5g of a white solid with a yield of 73%.
Other preferred compounds were the same as in synthesis example 1, except that the following compounds were used instead of the bromides and intermediates:
the characterization was performed by mass spectrometry and elemental analysis of compounds a1 to a26, and the data are shown in table 1.
The technical effects of the compounds of the present invention are explained in more detail below by means of device examples.
Comparative example 1
Carrying out ultrasonic treatment on the glass plate coated with the ITO transparent conductive layer in a commercial cleaning agent, washing the glass plate in deionized water, ultrasonically removing oil in an acetone-ethanol mixed solvent (the volume ratio is 1: 1), baking the glass plate in a clean environment until the water is completely removed, cleaning the glass plate by using ultraviolet light and ozone, and bombarding the surface by using low-energy cationic beams;
placing the glass substrate with the anode in a vacuum chamber, and vacuumizing to 1 × 10-5～9×10-3Pa, performing vacuum evaporation on the anode layer film to form 2-TNATA serving as a hole injection layer, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 10 nm;
NPB is evaporated on the hole injection layer in vacuum to serve as a hole transport layer of the device, the evaporation rate is 0.1nm/s, and the total film thickness of evaporation is 80 nm;
a luminescent layer of the device is evaporated on the hole transport layer in vacuum, the luminescent layer comprises a main material and a dye material, the evaporation rate of the main material ADN is adjusted to be 0.1nm/s, the evaporation rate of the dye C1 is set in a proportion of 3%, and the total film thickness of evaporation is 30nm by using a multi-source co-evaporation method;
vacuum evaporating an electron transport layer material Bphen of the device on the luminescent layer, wherein the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 30 nm;
LiF with the thickness of 0.5nm is vacuum-evaporated on the Electron Transport Layer (ETL) to be used as an electron injection layer, and an Al layer with the thickness of 150nm is used as a cathode of the device.
The organic electroluminescent device in the device comparison example has the following structure:
ITO/2-TNATA(10nm)/NPB(80nm)/EML(30nm)/Bphen(30nm)/LiF(1nm)/Al。
the molecular structure of each functional layer material is as follows:
comparative example 2
The procedure is identical to that of comparative example 1, except that NPB is replaced by an equal amount of comparative compound C2
Comparative example 3
The procedure is identical to that of comparative example 1, except that NPB is replaced by an equal amount of comparative compound C3
Device example 1
The method is the same as device example 1, except that NPB is replaced by an equal amount of A1
Device example 2
The procedure was the same as in device example 1, except that A1 was replaced with an equal amount of A3
Device example 3
The procedure was the same as in device example 1, except that A1 was replaced with an equal amount of A6
Device example 4
The procedure was the same as in device example 1, except that A1 was replaced with an equal amount of A11
Device example 5
The procedure was the same as in device example 1, except that A1 was replaced with an equal amount of A13
Device example 6
The procedure was the same as in device example 1, except that A1 was replaced with an equal amount of A19
Device example 7
The procedure was the same as in device example 1, except that A1 was replaced with an equal amount of A22
At the same luminance 1000cd/m2Next, the driving voltage and current efficiency of the organic electroluminescent device prepared in the device example were measured using a Keithley 2602 digital source meter luminance meter (peking university photoelectric instrument factory), and the corresponding performance indexes are detailed in table 2 below.
Table 2:
| serial number | HTL | Required luminance cd/m2 | Voltage V | Current efficiency cd/A |
| Device example 1 | A1 | 1000.00 | 5.6 | 8.3 |
| Device example 2 | A3 | 1000.00 | 5.7 | 8.6 |
| Device example 3 | A6 | 1000.00 | 5.5 | 8.2 |
| Device example 4 | A11 | 1000.00 | 5.5 | 8.3 |
| Device example 5 | A13 | 1000.00 | 5.4 | 8.9 |
| Device example 6 | A19 | 1000.00 | 5.6 | 8.4 |
| Device example 7 | A22 | 1000.00 | 5.5 | 8.4 |
| Comparative example 1 | NPB | 1000.00 | 6.3 | 6.2 |
| Comparative example 2 | C2 | 1000.00 | 5.9 | 6.0 |
| Comparative example 2 | C3 | 1000.00 | 5.5 | 5.2 |
As can be seen from the above table, the organic electroluminescent device using the arylamine compound of the present invention as a light emitting material can achieve a low voltage and a high luminous efficiency as compared to the organic electroluminescent device using NPB as a hole transport material,
the present invention has no great advantage in voltage, but is higher in efficiency than the prior art C2. The reason is not clear, and the following may be presumed: the methyl on the inner part of the parent nucleus of the compound C2 is not conjugated with molecules, plays a role in repulsion in molecular accumulation film formation and is not beneficial to the combination of intermolecular force; furthermore, the device itself is an environment filled with holes and electrons, and methyl in the environment is easy to generate free radicals to generate chemical reactions so as to generate other compounds, so that the material change causes the reduction of the efficiency life. Although methyl groups are also present in some preferred compounds of the invention, the methyl groups of the compounds of the invention are sterically insignificant in the peripheral space of the molecule and are not repulsive to intermolecular forces.
Although the invention has been described in connection with the embodiments, the invention is not limited to the embodiments described above, and it should be understood that various modifications and improvements can be made by those skilled in the art within the spirit of the invention, and the scope of the invention is outlined by the appended claims.
Claims (9)
1. A biphenyl diamine type triarylamine compound has a structure shown in the following general formula (I),
wherein Ar is1、Ar2Independently selected from:
the dotted line represents a bonding site to the N atom in the formula (I),
R1、R2independently selected from unsubstituted C3-C20Aryl of (a);
R3、R4、R5、R6、R7、R8、R9independently selected from: hydrogen, C1-C4Alkyl groups of (a);
R10、R11independently is selected from C1-C4Alkyl of (C)3-C6At least one of cycloalkyl, phenyl, biphenyl, terphenyl of (a);
each R is1、R2、R3、R4、R5、R6、R7、R8Or R9Not mutually connected to form a ring, and not condensed with adjacent benzene rings to form a ring;
n represents an integer of 0 to 3, m represents an integer of 0 to 5, p represents an integer of 0 to 7, q represents an integer of 0 to 4,
when n, m, p, and q are 2 or more, a plurality of R3、R4、R5、R6、R7、R8Or R9Each may be the same or different.
2. A compound according to claim 1, R1、R2Independently at least one unsubstituted phenyl group, biphenyl group, terphenyl group,
R3、R4、R5、R6、R7、R8、R9independently is selected from C1-C4At least one of alkyl groups of (a).
3. The compound according to claim 1 or 2, wherein,
R1and R2Same as R3And R4Same as R5And R6Same as R10And R11The same is true.
4. A compound, wherein,
the compound is selected from one of the following compounds:
5. a hole transport material comprising the compound according to any one of claims 1 to 4.
6. Use of a compound according to any one of claims 1 to 4 in an organic electroluminescent device.
7. An organic electroluminescent device comprising a substrate, a cathode, an anode and a hole transport layer between the cathode and the anode, the hole transport layer comprising the compound of any one of claims 1 to 4 or the hole transport material of claim 5.
8. An organic electroluminescent device comprising a substrate, a cathode, an anode and a hole injection layer between the cathode and the anode, the hole injection layer comprising the compound of any one of claims 1 to 4 or the hole transport material of claim 5.
9. The organic electroluminescent device according to claim 7 or 8, which has an anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer and a cathode in this order.
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| JP2011173973A (en) * | 2010-02-24 | 2011-09-08 | Toyo Ink Sc Holdings Co Ltd | Material for organic electroluminescent element and application thereof |
| US8716484B1 (en) * | 2012-12-05 | 2014-05-06 | Universal Display Corporation | Hole transporting materials with twisted aryl groups |
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